Chemistry of Renieramycins. Part 3. Isolation and Structure of Stabilized Renieramycin Type Derivatives Possessing Antitumor Activity from Thai Sponge Xestospongia Species, Pretreated with Potassium Cyanide

Journal of Natural Products

Volumn 66, Issue 11, 2003, Pages 1441-1446

  Suwanborirux, Khanit ^a   Amnuoypol, Surattana ^a   Plubrukarn, Anuchit ^b   Pummangura, Sunibhond ^a   Kubo, Akinori ^c   Tanaka, Chieko ^c   Saito, Naoki ^c  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b PRINCE OF SONGKLA UNIVERSITY   (Thailand)

^c MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POTASSIUM CYANIDE; RENIERAMYCIN DERIVATIVE; RENIERAMYCIN M; RENIERAMYCIN N; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; XESTOSPONGIA EXTRACT;

ANIMAL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG ISOLATION; DRUG STABILITY; DRUG STRUCTURE; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SPONGE (PORIFERA); STEREOCHEMISTRY; THAILAND; XESTOSPONGIA;

ANIMALIA; PORIFERA; XESTOSPONGIA;

EID: 0344118694     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030262p     Document Type: Article

References (29)

1. Part 2: Koizumi Y.; Kubo, A.; Suwanborirux, K.; Saito N. Heterocycles 2002, 57, 2345-2355.
2. McIntyre, D. E.; Faulkner, D. J.; Van Engen, D.; Clardy, J. Tetrahedron Lett. 1979, 4163-4166. Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265-269 (see Additions and Corrections: J. Am. Chem. Soc. 1983, 104, 5004). He, H.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5822-5824.
3. McIntyre, D. E.; Faulkner, D. J.; Van Engen, D.; Clardy, J. Tetrahedron Lett. 1979, 4163-4166. Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265-269 (see Additions and Corrections: J. Am. Chem. Soc. 1983, 104, 5004). He, H.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5822-5824.
4. McIntyre, D. E.; Faulkner, D. J.; Van Engen, D.; Clardy, J. Tetrahedron Lett. 1979, 4163-4166. Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265-269 (see Additions and Corrections: J. Am. Chem. Soc. 1983, 104, 5004). He, H.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5822-5824.
5. McIntyre, D. E.; Faulkner, D. J.; Van Engen, D.; Clardy, J. Tetrahedron Lett. 1979, 4163-4166. Frincke, J. M.; Faulkner, D. J. J. Am. Chem. Soc. 1982, 104, 265-269 (see Additions and Corrections: J. Am. Chem. Soc. 1983, 104, 5004). He, H.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5822-5824.
6. (b) Davidson, B. S. Tetrahedron Lett. 1992, 33, 3721-3724.
7. (c) Parameswarn, P. S.; Naik, C. G.; Kamat, S. Y.; Pramanik, B. N. Indian J. Chem. 1998, 37B, 1258-1263.
8. (d) Petitt, G. R.; Collins, J. C.; Herald, D. L.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A.; Tackett, L. P. Can. J. Chem. 1992, 70, 1170-1175. Pettit, G. R.; Knight, J. C.; Collins, J. C.; Herald, D. L.; Pettit, R. K.; Boyd, M. R.; Young, V. G. J. Nat. Prod. 2000, 63, 793-798.
9. (d) Petitt, G. R.; Collins, J. C.; Herald, D. L.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A.; Tackett, L. P. Can. J. Chem. 1992, 70, 1170-1175. Pettit, G. R.; Knight, J. C.; Collins, J. C.; Herald, D. L.; Pettit, R. K.; Boyd, M. R.; Young, V. G. J. Nat. Prod. 2000, 63, 793-798.
10. Fontana, A.; Cavaliere, P.; Wahidulla, S.; Naik, C. G.; Cimino, G. Tetrahedron 2000, 56, 7305-7308.
11. Arai, T.; Kubo, A. The Alkaloids: Brossi, A., Ed.; Academic: New York, 1983; Vol. 21, pp 55-100.
12. (b) Tomson, R. H. Naturally Occurring Quinones III; Chapman and Hall: New York, 1987; pp 633-686.
13. (c) Kubo, A.; Saito, N. Studies in Natural Products Chemistry: Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10, pp 77-145.
14. (d) Ozturk, T. The Alkaloids; Cordell, G. A., Ed.; Academic: New York, 2000; Vol. 53, pp 119-238.
15. (e) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 202, 1669-1730.
16. For previous work on the synthesis of renieramycins, see: (a) Fukuyama, T.; Linton, S. D.; Tun, M. M. Tetrahedron Lett. 1990, 31, 5989-5992.
17. (b) Saito, N.; Yamauchi, R.; Kubo, A. Heterocycles 1991, 32, 1203-1214.
18. Wright, A. E.; Forleo, D. A.; Gunawardana, G. P.; Gunasekera, S. P.; Koehn, F. K.; McConnel, J. M. J. Org. Chem. 1990, 55, 4508-4512.
19. (b) Rinehart, K. L.; Holt, T. G.; Fregeau, N. L.; Stroh, J. G.; Keifer, P. A.; Sun, F.; Li, L. H.; Martin, D. G. J. Org. Chem. 1990, 55, 4512-4515.
20. (c) Sakai, R.; Rinehart, K. L.; Guan, Y.; Wang, A. H.-J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11456-11460.
21. (d) Sakai, R.; Jares-Erijiman, E. A.; Manzanares, I.; Elipe, M. V. S.; Rinehart, K. L. J. Am. Chem. Soc. 1996, 118, 9017-9023.
22. Compounds 4-6 were identical with the synthesized ones on comparison of spectroscopic data and TLC; see: Kubo, A.; Nakahara, S.; Inaba, K.; Kitahara, Y. Chem. Pharm. Bull. 1986, 34, 4056-4068.
23. Edrada, R. A.; Proksch, P.; Wray, V.; Christ, R.; Witte, L.; Van Soest, R. W. M. J. Nat. Prod. 1996, 59, 973-976.
24. Structure of saframycin D, see: Kubo, A.; Saito, N.; Kitahara, Y.; Takahashi, K.; Yazawa, K.; Arai, T. Chem. Pharm. Bull. 1986, 35, 440-442.
25. (b) Structures of saframycins F and G, see: Mikami, Y.; Takahashi, K.; Yazawa, K.; Hour-Young, C.; Arat, T,; Saito, N.; Kubo, A. J. Antibiot. 1988, 41, 734-740.
26. The synthesis of 12 was reported in a separate paper; see ref 1.
27. 2, Pd/C, ethyl acetate followed by air oxidation) in 52% overall yield.
28. Structure of saframycin E, see: Saito, N.; Harada, S.; Nishida, M.; Inouye, I.; Kubo, A. Chem. Pharm. Bull. 1995, 43, 777-782.
29. While this paper was under review, Fusetani and co-workers reported a new renieramycin derivative 13, named renieramycin J, from a marine sponge Neopetrosia sp. collected in southern Japan; see: Oku, N.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Nat. Prod. 2003, 66, 1136-1139. However, we have already named structures 1j-1 renieramycins J-L, respectively. Thus structure 13, named renieramycin J by the Fusetani group, should be renamed renieramycin P.